Building @askumbrella. Previously building products, teams, and companies at @sidewalklabs & @imgur, investing at @a16z http://samgerstenzang.com

Dec 31, 2017

17 lessons I learned in 2017

2017 ended up being a year of tremendous growth, after what I now realize was a year of terrifying stagnation.

In 2017, I started a new company, moved to a new apartment, fell in love, started seeing a coach regularly (highly recommended), experienced loss, began developing a practice of presence, and more.

In creating resolutions for the new year, I revisited 2017’s resolutions which I hadn’t looked at since I constructed them. Some of them I had surpassed effortlessly, others were completely untouched. But the most important things I’ve done or learned in this last year weren’t on the list.

On ego and work

Separate your identity from your work on macro level. When you start a company (or do anything that feels important), it can feel like it will become you. This was a difficult barrier to get over: is this the thing that can define my life? But that’s not how it works. This next project might take one year, five, or twenty, but it is not you. You are a superset of what you do, not a subset.

Separate your identity from your work on a micro level. You are not your ideas; ideas come through us and our job is to let them go. If you overlap your identity with your ideas, you risk feeling they are each precious, and of feeling criticized when your ideas are wrong or said to be wrong. If you can separate yourself from your ideas, the work will be better.

I realized my highest calling was not making the best work but producing the best work. Sometimes I’m the most talented individual contributor for a certain part of a certain kind of project. But most often I’m not. In both cases, my job is the same: how do I use the other talents inside and out of the room to create the best output?

Ultimately, we will not find happiness from the output of our work (which is static and fleeting), only in its process (which is continuous).

On work, growth, and victory

One way to win, or to make losing sufferable, is to change the time scale of victory. When others are thinking in weeks or months, think in years and decades. When others are thinking in years, use days and hours.

The real work is in the day-to-day details. That’s what consumes your life. Make sure you enjoy it. Too often we are interested in the arc of things rather than their pillars.The most fulfilling job will have both an arc (e.g. human psychology) and the pillars (e.g. the daily work of clinical care, research, etc.) that consume you.

We tend to define ourselves in personal narratives. I’m terrible at parties. I’m always late. Two ideas: 1) Create narratives for good. Allow yourself to tell the story of how you changed to become more like the you that you would like to be. 2) Narratives based in past behavior are by definition out of date. Sometimes allow yourself to just be open to possibility of the next moment being different. How does the story change in this moment?

Luck can’t be controlled, but your exposure to allow luck to strike can be. Work hard to increase your surface area.

The key to talent development of yourself and others: propulsion off cliffs with parachutes one size too small. Sometimes you land hard but your wings build muscle.

Previously, one of the skills I’d valued was finding arbitrages created by others’ bias. Bias against the unproven, against the old, against the boring: there are great discounts to be found in hires, investments, and in life. But one corollary I learned this year: the size of the discount doesn’t matter if you’re chasing a small opportunity. I’d much rather own 20% of something at 10% discount going to 10,000 than 20% of something at 50% discount going to 100.

On being present, emotions, and thinking

We don’t see people as they are, we see them as we are. This sounds simple but in it we find the root of all human conflict.

Meaning is created only within ourselves. This should be both terrifying and greatly freeing. Find your personal meaning and live your life for it.

Only the present exists. The past and future are fictional; they exist only in our minds. (I highly recommend The Power of Now for more.)

It is not the mind’s job to deal with feelings. You don’t need to rationalize them. Feelings are for all the information we cannot process. In general, we overrate thinking as a positive human attribute.

At the same time, thoughts do lead to feelings. Developing the skill of annotating your feelings as they occur is a powerful tool that will make you both happier and more in control.

You can use the irritants and suffering in your life to become your best self. Think of these as great gifts with which you can use to understand yourself, the sand to create your personal pearl.

The good things all have trade-offs. It is better to think in trade-offs than in dualities: there is not a best lens. How do you maximize the good parts while cushioning the bad parts of one particular lens? And then what do you get from another lens altogether? There is rarely one lens that will get you where you need to go, but each lens will bring you to a different place.